Showing Metabocard for androst-4-ene-3,17-dione (BASm0000617)

Common NameAndrost-4-ene-3,17-dione
DescriptionAndrostenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while the production of gonadal androstenedione is under control by gonadotropins.
Structure
Molecular FormulaC19H26O2
Average Mass286.40850
Monoisotopic Mass286.19328
IUPAC Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Traditional Name4-androstenedione
CAS Registry Number1963-05-08
SMILESC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChI IdentifierInChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChI KeyAEMFNILZOJDQLW-QAGGRKNESA-N
CHEBI IDCHEBI:16422
HMDB IDHMDB0000053
Pathways
NameSMPDB/PathBank
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Aromatase deficiency
Androstenedione Metabolism
StateNot Available
Water Solubility2.70e-02 g/l
logP2.93
logS-4.03
pKa (Strongest Acidic)19.03
pKa (Strongest Basic)-4.82
Hydrogen Acceptor Count2
Hydrogen Donor Count0
Polar Surface Area34.14 Ų
Rotatable Bond Count0
Physiological Charge0
Formal Charge0
Refractivity83.61 m³·mol⁻¹
Polarizability33.05

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